Triethylamine → CCK antagonist synthetic 21

HRID 1084531Notes

Reaction equation

HRID 1084531 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:20].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[C:30](Cl)=[O:31].C(N(CC)CC)C>C(Cl)Cl>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3](=[O:20])[CH:2]([NH:1][C:30]([C:22]2[NH:21][C:29]3[C:24]([CH:23]=2)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:31])[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118162081H-indole-2-carbonyl ChlorideHCID 156371501,3-dihydro-5-(2-fluorophenyl)-3-amino-2H-1,4-benzodiazepin-2-one

Product 1

HCID 10476766CCK antagonist synthetic 21

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(RS)-Amino-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (1.5 gm, 5.57 mmol), indole-2-carbonyl chloride (1.05 gm, 5.85 mmol) and triethylamine (0.814 ml, 5.85 mmol) were combined in CH2Cl2 (15 ml) and stirred 10 min. The reaction was concentrated and chromatographed on silica gel (5% MeOH in CH2Cl2) to give the title compound as a white solid from CH2Cl2 : (m.p. 290°-291°).

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed on silica gel (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9b2ee5c14ba547a7a10747a43d8f0b02
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

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